Shelter Island Vacations from ₩2,025,692

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The Latest Shelter Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
OYO Times Square

OYO Times Square

4 out of 5
Manhattan
Price was ₩2,807,568, price is now ₩2,025,692 per person
₩2,025,692
per person
Apr 22 - Apr 28
found 13 hours ago
Roundtrip flight included
Seoul (ICN) to Newark Liberty Intl. Airport (EWR)
7/10 Good! (1,782 reviews)
Property was ok. You would hear doors slamming all through the night but I really was ok.

Reviewed on Mar 23, 2026

PUBLIC, an Ian Schrager hotel

PUBLIC, an Ian Schrager hotel

4 out of 5
Manhattan
Price was ₩3,497,190, price is now ₩2,745,860 per person
₩2,745,860
per person
Apr 22 - Apr 28
found 13 hours ago
Roundtrip flight included
Seoul (ICN) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (3,443 reviews)
Great hotel! The room was very clean. The dining rooms and bars were fun, great food and drinks, great service. Awesome location. Great experience.

Reviewed on Mar 23, 2026

Pod Times Square

Pod Times Square

3 out of 5
Manhattan
Price was ₩2,385,223, price is now ₩2,077,136 per person
₩2,077,136
per person
Apr 22 - Apr 28
found 13 hours ago
Roundtrip flight included
Seoul (ICN) to Newark Liberty Intl. Airport (EWR)
9/10 Wonderful! (5,342 reviews)
Perfect location, affordable, nice spot

Reviewed on Mar 23, 2026

Where to stay in Shelter Island

Find the best Shelter Island areas and neighborhoods for the activities you enjoy most. Learn more about Shelter Island
Center console boat on Long Island, NY. Photographed by drone.

Silver Beach

While Silver Beach might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Sunset Beach and Crescent Beach.

Find hotels in Silver Beach

Find the Best Shelter Island Vacation Packages

Shelter Island Beach Vacation

There's nothing like a Shelter Island vacation to give you a little extra bounce in your step. The sound of rolling surf and the smell of clean ocean air are sure to refresh your mind, body and soul. To be close to the town center on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometers away). If you're planning to stay for a bit, look into our Shelter Island packages. Not only can you save some cash, you'll also have other amazing beaches near you to explore, like Shell Beach and Menhadden Lane Beach.

Shelter Island Hotel Deals

Gurney's Montauk Resort & Seawater Spa

Gurney's Montauk Resort & Seawater Spa

4 out of 5
290 Old Montauk Highway Montauk NY
The price is ₩575,203 per night from Mar 24 to Mar 25
₩575,203
₩788,602 total
Mar 24 - Mar 25
includes taxes & fees
8.4/10 Very Good! (742 reviews)
We booked this hotel for the indoor pool so the kids can spend their time swimming, upon arrival we were asked if we received a call that the pool will be closed due to maintenance(which we did not)This was extremely frustrating as the pool was the reason that we booked the hotel. They offered to ...

Reviewed on Mar 23, 2026

Gurney's Montauk Resort & Seawater Spa
Montauk Manor

Montauk Manor

3.5 out of 5
236 Edgemere St. Montauk NY
The price is ₩227,375 per night from Mar 24 to Mar 25
₩227,375
₩289,241 total
Mar 24 - Mar 25
includes taxes & fees
9.2/10 Wonderful! (1,307 reviews)
Everything was lovely. It was a wonderful place to relax after a long day of sightseeing.

Reviewed on Mar 23, 2026

Montauk Manor
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Fully refundableReserve now, pay when you stay
The price is ₩293,882 per night from Mar 25 to Mar 26
₩293,882
₩363,904 total
Mar 25 - Mar 26
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
Everything was excellent! My only comment is that there were many piles of roomservice dishes left in the hallway for over 24 hours ( not mine)

Reviewed on Mar 22, 2026

Water's Edge Resort & Spa
See all 4,741 properties in Shelter Island
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Discover the most popular places to visit in Shelter Island

Havens House

You can spend an afternoon browsing the exhibits at Havens House during your trip to Shelter Island. Stroll along the area's beaches or simply enjoy its wineries.

Havens House

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.